1-phenyl-3-methyl-4-p-bromobenzoyl-pyrazol-5-one | 31197-07-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-phenyl-3-methyl-4-p-bromobenzoyl-pyrazol-5-one
• 英文别名: 4-[(4-bromophenyl)carbonyl]-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one；4-(4-bromobenzoyl)-5-methyl-2-phenyl-4H-pyrazol-3-one
• CAS: 31197-07-6
• 化学式: C₁₇H₁₃BrN₂O₂
• 分子量: 357.206
• InChiKey: VFKBNGYRTCIFOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-phenyl-3-methyl-4-p-bromobenzoyl-pyrazol-5-one 、 tin(ll) chloride 在 KOH 作用下， 以 甲醇 为溶剂， 以88%的产率得到bis(1-phenyl-3-methyl-4-p-bromobenzoyl-pyrazolon-5-ato)tin(II)
  参考文献：
  名称：

  Synthesis and characterization of some tin(II) and tin(IV) derivatives of 4-acyl-5-pyrazolones. Crystal structure of bis(1-phenyl-3-methyl-4-acetyl-pyrazolon-5-ato)tin(II)

  摘要：

  Stable, four-coordinated (Q)2Sn compounds have been prepared, where QH is 1-phenyl-3-methyl-4-RC(=O)-pyrazol-5-one (R = CH3, CF3, n-C6H13, C6H5, p-F-C6H4, p-Cl-C6H4, p-Br-C6H4, p-I-C6H4, p-NO2-C6H4, p-CH3O-C6H4). They have been characterized through analytical data, IR and H-1, C-13 and Sn-119 NMR spectroscopy. In the crystal structure of the title compound (8), the tin atom is found in a distorted psi trigonal bipyramidal environment, with the tin lone pair occupying an equatorial site. The diaxial angle O-Sn-O is bent [149.8(2)2)degrees] and two sets of Sn-O distances are found [Sn-O(1) = 2.141 (5) angstrom; Sn-O(3) = 2.133 (5) angstrom; Sn-O(2) = 2.296 (6) angstrom; Sn-O(4) = 2.313 (6) angstrom. Oxidative addition of iodomethane or dihalogens (Br2 or I2) to (Q)2Sn provides a route to new (Q)2R(n)Sn(IV)X2-n compounds (where X = Br or I; R = CH3 or X).

  DOI：

  10.1016/s0277-5387(00)83014-4

文献信息

• Novel mixed ligand di-n-butyltin(IV) complexes derived from acylpyrazolones and fluorinated benzoic acids: Synthesis, characterization, cytotoxicity and the induction of apoptosis in Hela cancer cells
  作者：Bin Zhao、Xianmei Shang、Ling Xu、Wendian Zhang、Guangya Xiang

  DOI：10.1016/j.ejmech.2014.02.039

  日期：2014.4

  Twenty one novel mixed ligand di-n-butyltin(IV) complexes [(n)Bu(2)SnAL] (A = substituted 4-acyl-5-pyrazolone, and L = fluorinated benzoic acid) were prepared by condensation of di-n-butyltin(IV) oxide with HL and HA in 1:1:1 molar ratio in refluxing methanol. All of the complexes were characterized by elemental analyses, IR, NMR (H-1, C-13, Sn-119) and in four cases by X-ray diffraction. Cytotoxicity of the compounds was studied against two human cancer cell lines (KB and Hela) by means of the MU assay compared to cisplatin, featuring IC50 values in the low micromolar range. Hela cancer cell apoptosis-induced by 2 was examined by flow cytometry analysis, and preliminary results showed that 2 at concentrations of more than 1.0 mu M can induce apoptosis. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Synthesis and characterization of some tin(II) and tin(IV) derivatives of 4-acyl-5-pyrazolones. Crystal structure of bis(1-phenyl-3-methyl-4-acetyl-pyrazolon-5-ato)tin(II)
  作者：Claudio Pettinari、Fabio Marchetti、Augusto Cingolani、Clara Marciante、Riccardo Spagna、Marcello Colapietro

  DOI：10.1016/s0277-5387(00)83014-4

  日期：1994.3

  Stable, four-coordinated (Q)2Sn compounds have been prepared, where QH is 1-phenyl-3-methyl-4-RC(=O)-pyrazol-5-one (R = CH3, CF3, n-C6H13, C6H5, p-F-C6H4, p-Cl-C6H4, p-Br-C6H4, p-I-C6H4, p-NO2-C6H4, p-CH3O-C6H4). They have been characterized through analytical data, IR and H-1, C-13 and Sn-119 NMR spectroscopy. In the crystal structure of the title compound (8), the tin atom is found in a distorted psi trigonal bipyramidal environment, with the tin lone pair occupying an equatorial site. The diaxial angle O-Sn-O is bent [149.8(2)2)degrees] and two sets of Sn-O distances are found [Sn-O(1) = 2.141 (5) angstrom; Sn-O(3) = 2.133 (5) angstrom; Sn-O(2) = 2.296 (6) angstrom; Sn-O(4) = 2.313 (6) angstrom. Oxidative addition of iodomethane or dihalogens (Br2 or I2) to (Q)2Sn provides a route to new (Q)2R(n)Sn(IV)X2-n compounds (where X = Br or I; R = CH3 or X).